[ CAS No. 3188-00-9 ] {[proInfo.proName]}

Name: 3188-00-9|2-Methyltetrahydrofuran-3-one|98%
Brand: Ambeed
SKU: A312941
Price: 5.0 USD
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Quality Control of [ 3188-00-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 3188-00-9 ]

Product Details of [ 3188-00-9 ]

CAS No. :	3188-00-9	MDL No. :	MFCD00010423
Formula :	C₅H₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FCWYQRVIQDNGBI-UHFFFAOYSA-N
M.W :	100.12	Pubchem ID :	18522
Synonyms :

Calculated chemistry of [ 3188-00-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.8
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	25.32
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.89 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.43
Log Po/w (XLOGP3) :	0.03
Log Po/w (WLOGP) :	0.36
Log Po/w (MLOGP) :	-0.31
Log Po/w (SILICOS-IT) :	1.32
Consensus Log Po/w :	0.57

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.48
Solubility :	33.2 mg/ml ; 0.331 mol/l
Class :	Very soluble
Log S (Ali) :	-0.13
Solubility :	73.4 mg/ml ; 0.733 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.7
Solubility :	20.2 mg/ml ; 0.201 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.76

Safety of [ 3188-00-9 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P305+P351+P338	UN#:	1224
Hazard Statements:	H225-H302	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 3188-00-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 3188-00-9 ]
Downstream synthetic route of [ 3188-00-9 ]

[ 3188-00-9 ] Synthesis Path-Upstream 1~16

1
[ 517-23-7 ]
[ 3188-00-9 ]

Reference： [1] Synthetic Communications, 1998, vol. 28, # 22, p. 4273 - 4278

2
[ 86040-09-7 ]
[ 3188-00-9 ]

Reference： [1] Tetrahedron Letters, 1984, vol. 25, # 48, p. 5567 - 5570

3
[ 95510-97-7 ]
[ 3188-00-9 ]

Reference： [1] Tetrahedron Letters, 1984, vol. 25, # 48, p. 5567 - 5570

4
[ 58-86-6 ]
[ 59-43-8 ]
[ 74015-70-6 ]
[ 137-00-8 ]
[ 3188-00-9 ]
[ 40789-98-8 ]
[ 67633-97-0 ]
[ 28588-74-1 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556

5
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[ 59-43-8 ]
[ 74015-70-6 ]
[ 137-00-8 ]
[ 3188-00-9 ]
[ 40789-98-8 ]
[ 67633-97-0 ]
[ 28588-74-1 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556

6
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[ 52-90-4 ]
[ 59-43-8 ]
[ 98-01-1 ]
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[ 3188-00-9 ]
[ 40789-98-8 ]
[ 67633-97-0 ]
[ 98-02-2 ]
[ 63012-97-5 ]
[ 28588-74-1 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556
[2] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556
[3] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556

7
[ 58-86-6 ]
[ 52-90-4 ]
[ 59-43-8 ]
[ 74015-70-6 ]
[ 137-00-8 ]
[ 3188-00-9 ]
[ 40789-98-8 ]
[ 67633-97-0 ]
[ 98-02-2 ]
[ 63012-97-5 ]
[ 28588-74-1 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556

8
[ 28564-83-2 ]
[ 3658-77-3 ]
[ 1073-96-7 ]
[ 3188-00-9 ]
[ 600-14-6 ]
[ 80-71-7 ]
[ 116-09-6 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 1996, vol. 44, # 1, p. 282 - 289

9
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[ 1262683-58-8 ]
[ 59-43-8 ]
[ 3188-00-9 ]
[ 40789-98-8 ]
[ 67633-97-0 ]
[ 63012-97-5 ]
[ 28588-74-1 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556

10
[ 52-90-4 ]
[ 1262683-58-8 ]
[ 59-43-8 ]
[ 3188-00-9 ]
[ 40789-98-8 ]
[ 67633-97-0 ]
[ 63012-97-5 ]
[ 28588-74-1 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556

11
[ 50-81-7 ]
[ 1192-62-7 ]
[ 930-68-7 ]
[ 3188-00-9 ]
[ 10493-98-8 ]
[ 23033-96-7 ]
[ 431-03-8 ]

Reference： [1] Carbohydrate Research, 1997, vol. 305, # 1, p. 1 - 15

12
[ 50-81-7 ]
[ 1192-62-7 ]
[ 930-68-7 ]
[ 3188-00-9 ]
[ 10493-98-8 ]
[ 23033-96-7 ]
[ 431-03-8 ]

Reference： [1] Carbohydrate Research, 1997, vol. 305, # 1, p. 1 - 15

13
[ 58-86-6 ]
[ 52-90-4 ]
[ 59-43-8 ]
[ 98-01-1 ]
[ 137-00-8 ]
[ 3188-00-9 ]
[ 40789-98-8 ]
[ 67633-97-0 ]
[ 98-02-2 ]
[ 63012-97-5 ]
[ 28588-74-1 ]

14
[ 58-86-6 ]
[ 52-90-4 ]
[ 59-43-8 ]
[ 74015-70-6 ]
[ 137-00-8 ]
[ 3188-00-9 ]
[ 40789-98-8 ]
[ 67633-97-0 ]
[ 98-02-2 ]
[ 63012-97-5 ]
[ 28588-74-1 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556

15
[ 52-90-4 ]
[ 1262683-58-8 ]
[ 59-43-8 ]
[ 3188-00-9 ]
[ 40789-98-8 ]
[ 67633-97-0 ]
[ 63012-97-5 ]
[ 28588-74-1 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556

16
[ 52-90-4 ]
[ 1262683-58-8 ]
[ 59-43-8 ]
[ 3188-00-9 ]
[ 40789-98-8 ]
[ 67633-97-0 ]
[ 63012-97-5 ]
[ 28588-74-1 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556

[ 3188-00-9 ] Synthesis Path-Downstream 1~97

1
[ 75-77-4 ]
[ 3188-00-9 ]
2-methyl-3-trimethylsilyloxy-2,5-dihydrofuran [ No CAS ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 2925 - 2934

2
[ 75-97-8 ]
[ 3188-00-9 ]
(+/-)-1-<(1SR,2SR)-1-hydroxy-2-methyl-3-oxacyclopentyl>-3,3-dimethyl-2-butanone [ No CAS ]
(+/-)-1-<(1SR,2RS)-1-hydroxy-2-methyl-3-oxacyclopentyl>-3,3-dimethyl-2-butanone [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1993,vol. 115,p. 1302 - 1312

3
[ 3188-00-9 ]
[ 3886-69-9 ]
[ 132902-45-5 ]

Reference： [1]Tetrahedron Asymmetry,1990,vol. 1,p. 759 - 762
[2]Enantiomer,2001,vol. 6,p. 289 - 298

4
[ 3188-00-9 ]
[ 3886-69-9 ]
[ 132902-45-5 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 2925 - 2934

5
[ 3188-00-9 ]
[ 20086-87-7 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1999,vol. 153-154,p. 303 - 304
[2]Journal of Medicinal Chemistry,1994,vol. 37,p. 1177 - 1188

6
[ 95510-97-7 ]
[ 3188-00-9 ]

Reference： [1]Tetrahedron Letters,1984,vol. 25,p. 5567 - 5570

7
[ 28564-83-2 ]
[ 3658-77-3 ]
[ 1073-96-7 ]
[ 3188-00-9 ]
[ 600-14-6 ]
[ 80-71-7 ]
[ 116-09-6 ]

Reference： [1]Journal of Agricultural and Food Chemistry,1996,vol. 44,p. 282 - 289

8
[ 50-81-7 ]
[ 1192-62-7 ]
[ 930-68-7 ]
[ 3188-00-9 ]
[ 10493-98-8 ]
[ 23033-96-7 ]
[ 431-03-8 ]

Reference： [1]Carbohydrate Research,1997,vol. 305,p. 1 - 15

9
[ 517-23-7 ]
[ 3188-00-9 ]

Reference： [1]Synthetic Communications,1998,vol. 28,p. 4273 - 4278

12
[ 3188-00-9 ]
[ 506-59-2 ]
(3S*)-N,N-dimethylamino-(2S*)-methyltetrahydrofuran [ No CAS ]
(3S*)-N,N-dimethylamino-(2R*)-methyltetrahydrofuran [ No CAS ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 4117 - 4128

13
[ 3188-00-9 ]
2-methyl-dihydro-furan-3-one oxime [ No CAS ]

Reference： [1]Scientia Pharmaceutica,2000,vol. 68,p. 101 - 108
[2]Angewandte Chemie - International Edition,2018,vol. 57,p. 738 - 743
Angew. Chem.,2018,vol. 130,p. 746 - 751,6
[3]Chemical Communications,2018,vol. 54,p. 12262 - 12265
[4]Organic Letters,2019,vol. 21,p. 2658 - 2662
[5]European Journal of Organic Chemistry,2020,vol. 2020,p. 1439 - 1442

14
[ 3188-00-9 ]
TosMIC [ No CAS ]
(3S*)-cyano-(2S*)-methyltetrahydrofuran [ No CAS ]
(3S*)-cyano-(2R*)-methyltetrahydrofuran [ No CAS ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 4117 - 4128

15
[ 3188-00-9 ]
[ 67-66-3 ]
[ 131179-77-6 ]
3-{4-[(3,5-dimethyl-phenylcarbamoyl)-methyl]-phenoxy}-2-methyl-tetrahydro-furan-3-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4726 - 4737

16
[ 3188-00-9 ]
[ 35737-15-6 ]
C₁₇H₂₀N₂O₃ [ No CAS ]
C₁₇H₂₀N₂O₃ [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4923 - 4926

17
[ 5162-44-7 ]
[ 3188-00-9 ]
3-(but-3-enyl)tetrahydro-2-methylfuran-3-ol [ No CAS ]

Reference： [1]Helvetica Chimica Acta,2004,vol. 87,p. 2750 - 2763

18
[ 3188-00-9 ]
[ 74-90-8 ]
3-hydroxy-2-methyltetrahydrofuran-3-carbonitrile [ No CAS ]
3-hydroxy-2-methyltetrahydrofuran-3-carbonitrile [ No CAS ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 10411 - 10418

19
[ 3188-00-9 ]
[ 105-56-6 ]
[ 1010798-34-1 ]

Yield	Reaction Conditions	Operation in experiment
	With morpholine; sulfur; at 50 - 60℃;	Example 1A; 2-amino-4-methyl-4,6-dihydrothieno[2,3-c]furan-3-carboxylic acid ethyl ester; To a 500-mL, round-bottomed flask containing a magnetic stir bar were added 2-methyltetrahydro-furan-3-one (10.0 g, 100 mmol), ethyl cyanoacetate (12.4 g, 11.7 mL, 110 mmol), and sulfur powder (3.53 g, 110 mmol). The mixture was stirred to form a yellow slurry and morpholine (13.1 g, 13.1 mL, 150 mmol) was added. A reflux condenser with N2 inlet was attached and a heating mantle was applied. The mixture was heated to 50-60 C. and stirred overnight. After cooling to room temperature, the volatiles were removed under reduced pressure. The residue was purified by flash chromatography (silica gel: 25% ethyl acetate in hexanes, Rf-0.3) to provide the title compound. 1H NMR (DMSO-d6, 300 MHz) delta 1.24 (t, J=7.1 Hz, 3H), 1.33 (d, J=6.1 Hz, 3H), 4.06-4.25 (m, 2H), 4.68 (dd, J=10.8, 2.0 Hz, 1H), 4.82 (dd, J=10.8, 4.6 Hz, 1H), 5.05-5.15 (m, 1H), 7.34 (br s, 2H); MS (ESI+) m/z 228 (M+H)+. Anal. calcd. for C20H17F4NO4S: C, 54.17; H, 3.86; N, 3.16. Found: C, 54.17; H, 3.78; N, 3.13.

Reference： [1]Patent: US2008/58308,2008,A1 .Location in patent: Page/Page column 11
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7314 - 7321

20
[ 3188-00-9 ]
[ 95-92-1 ]
C₉H₁₂O₅ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4914 - 4919

21
[ 3188-00-9 ]
C₉H₁₂N₂O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4914 - 4919

22
[ 3188-00-9 ]
C₇H₈N₂O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4914 - 4919

23
[ 3188-00-9 ]
(+/-)-(3aRS,6RS,7aRS)-octahydro-7a-methylbenzofuran-6-yl formate [ No CAS ]

Reference： [1]Helvetica Chimica Acta,2004,vol. 87,p. 2750 - 2763

24
[ 3188-00-9 ]
[ 41763-94-4 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1999,vol. 153-154,p. 303 - 304

25
[ 3188-00-9 ]
(2S,3S)-cis-2-methyl-3-hydroxytetrahydrofuran [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1999,vol. 153-154,p. 303 - 304

26
[ 3188-00-9 ]
(2S,3R)-2-methyl-tetrahydrofuran-3-thiol [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1999,vol. 153-154,p. 303 - 304
[2]Phosphorus, Sulfur and Silicon and the Related Elements,1999,vol. 153-154,p. 303 - 304

27
[ 3188-00-9 ]
(2R,3S)-2-methyl-tetrahydrofuran-3-thiol [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1999,vol. 153-154,p. 303 - 304

28
[ 3188-00-9 ]
2-methyltetrahydrofuran-3-amine [ No CAS ]

Reference： [1]Scientia Pharmaceutica,2000,vol. 68,p. 101 - 108

29
[ 3188-00-9 ]
[(1S,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propyl]-carbamic acid (2R,3R)-2-methyl-tetrahydro-furan-3-yl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1177 - 1188

30
[ 3188-00-9 ]
[(1S,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propyl]-carbamic acid (2S,3S)-2-methyl-tetrahydro-furan-3-yl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1177 - 1188

31
[ 3188-00-9 ]
Carbonic acid (2S,3S)-2-methyl-tetrahydro-furan-3-yl ester pyridin-2-yl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1177 - 1188

32
[ 86040-09-7 ]
[ 3188-00-9 ]

Reference： [1]Tetrahedron Letters,1984,vol. 25,p. 5567 - 5570

33
[ 3188-00-9 ]
[ 132902-51-3 ]

Reference： [1]Tetrahedron Asymmetry,1990,vol. 1,p. 759 - 762

34
[ 3188-00-9 ]
[ 132902-52-4 ]

Reference： [1]Tetrahedron Asymmetry,1990,vol. 1,p. 759 - 762

35
[ 3188-00-9 ]
[ 156-57-0 ]
[ 165261-13-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water;	Example 1 Synthesis of 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]Nonane To 15.4 g of 2-aminoethanethiol-HCl (0.13 mole) dissolved into 50 ml of water were added slowly 20 g of 2-methyl-3-tetrahydrofuranone (0.2 mole) (solution pH=2.7). The pH was kept to neutrality by adding 10% aqueous NaOH. After 1 hour, extraction of the water solution with Et2O, drying of the organic phase with MgSO4 and distillation of the crude product (Bp 1.7 mbar, 93-96 C.) gave 18 g of the desired product (yield=90%). The product was obtained as a mixture of two diastereoisomers (isomers a and b). 1H-NMR: 1.24(d, J=6.5, 3H, 56%; isomer a); 1.26(d, J=6.5, 3H, 44%; isomer b); 1.7(broad, 1H); 2.12-2.23(m, 1H); 2.30-2.41(m, 1H); 2.87-3.06(m, 2H); 3.19-3.39(m, 2H); 3.81-4.1(m, 3H). 13C-NMR: 86.4-83.7(s); 81.2-81.9(d); 65.8-65.5(t); 52.2-51.1(t); 43.3-41.4(t); 36.2-36.0(t); 13.3-19.6(q). MS: Isomer a: 159((M+H)+; 25), 130(10), 116(20), 115(96), 114(100), 87(10), 62(20), 60(25), 54(15), 43(10). Isomer b: 159((M+H)+; 25), 130(10), 116(20), 115(100), 114(98), 87(10), 62(20), 60(25), 54(15), 43(10).

Reference： [1]Patent: US2003/175395,2003,A1

36
[ 3188-00-9 ]
t-butyl dimethyl phosphonoacetate [ No CAS ]
[ 362700-75-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	In N,N-dimethyl-formamide;	N-{3-[2-(hydroxyamino)-2-oxoethyl]-2-methyltetrahydro-3-furanyl}-4-[(2-methyl-4-quinolinyl)methoxy]benzamide trifluoroacetate (365a) Following a procedure analogous to that used in reaction (364a-c), but using 2-methyl tetrahydrofuran-3-one and t-butyl dimethyl phosphonoacetate in DMF with sodium hydride, to prepare the alpha,beta-unsaturated ester. This ester was converted by procedures analogous to reactions (330b) and (330c), to give the title compound (0.208 g. 83%) as a mixture diastereomers, MS (M+H)+=450.

Reference： [1]Patent: US2002/13341,2002,A1

37
[ 3188-00-9 ]
trans-2-METHYL-3-TETRAHYDROFURYLAMINE [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.6 g (59%)	In methanol; hydrogen;	This amine was obtained following the method of Scheme 35. To 1.15 g (10 mmol) of <strong>[3188-00-9]2-methyltetrahydrofuran-3-one</strong> oxime (prepared via standard procedures from commercially available <strong>[3188-00-9]2-methyltetrahydrofuran-3-one</strong>) in 50 mL of methanol was added 1 g (wet weight) of Raney nickel that had been washed 3 times each with water and ethanol, and placed in a Parr shaker under 44 psig of hydrogen. After 18 hours, the mixture was vented and gravity filtered. The methanol was evaporated under vacuum, and the residue was taken up in ether and dried. The ethereal phase was evaporated under vacuum to give 0.6 g (59%) of the title amine 128 as a cis/trans mixture.

Reference： [1]Patent: US6355660,2002,B1

38
4'-{5-fluoro-3-[(2RS,3SR)-3-methoxy-2-methyltetrahydrofuran-3-yl]phenylthio}acetophenone [ No CAS ]
[ 3188-00-9 ]
[ 461-96-1 ]
[ 62351-47-7 ]
[ 106-93-4 ]
(2RS,3SR)-3-(3,5-difluorophenyl)-3-hydroxy-2-methyltetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With magnesium; In tetrahydrofuran;	The 4'-{5-fluoro-3-[(2RS,3SR)-3-methoxy-2-methyltetrahydrofuran-3-yl]phenylthio}acetophenone used as a starting material was obtained as follows: A solution of <strong>[3188-00-9]2-methyltetrahydrofuran-3-one</strong> (18.4 g) in THF (30 ml) was added to a THF solution of 3,5-difluorophenylmagnesium bromide [prepared by the addition of magnesium (4.8 g) to a mixture of 3,5-difluorobromobenzene (31 g), 1,2-dibromoethane (0.3 g) and THF (60 ml)]. The mixture was stirred at ambient temperature for 3 hours. The mixture was partitioned between ethyl acetate and a saturated aqueous ammonium chloride solution. The organic phase was washed with water and with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography using increasingly polar mixtures of hexane and ethyl acetate as eluent. There was thus obtained (2RS,3SR)-3-(3,5-difluorophenyl)-3-hydroxy-2-methyltetrahydrofuran (16.3 g, 38%), m.p. 89-90 C.

Reference： [1]Patent: US5332757,1994,A

39
[ 109-72-8 ]
[ 5053-24-7 ]
[ 3188-00-9 ]
(2RS,3RS)-3-hydroxy-2-methyl-3-(2-methylthiothiazol-5-yl)tetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	In tetrahydrofuran; hexane;	n-Butyl-lithium (1.6M in hexane, 87 ml) was added to a stirred solution of 2-methylthiothiazole (13.1 g) in THF (80 ml) which had been cooled to 0 C. The mixture was stirred at 0 C. for 75 minutes. A solution of <strong>[3188-00-9]2-methyltetrahydrofuran-3-one</strong> (11.95 g) in THF (30 ml) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was partitioned between diethyl ether and a saturated aqueous ammonium chloride solution. The organic phase was washed with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography using a 2:1 mixture of hexane and ethyl acetate as eluent. There was thus obtained (2RS,3RS)-3-hydroxy-2-methyl-3-(2-methylthiothiazol-5-yl)tetrahydrofuran (15.5 g, 67%), m.p. 79-80 C.

Reference： [1]Patent: US5332757,1994,A

40
[ 109-72-8 ]
[ 3188-00-9 ]
(2RS,3SR)-3-hydroxy-2-methyl-3-(2-methylthiothien-4-yl)tetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	In tetrahydrofuran; diethyl ether;	n-Butyl-lithium (1.6M in THF, 18.5 ml) was added to a stirred solution of the material so obtained in diethyl ether (100 ml) which had been cooled to -70 C. After 15 minutes, a solution of <strong>[3188-00-9]2-methyltetrahydrofuran-3-one</strong> (3 g) in diethyl ether (8 ml) was added. The mixture was stirred at -70 C. for 30 minutes and then allowed to warm to ambient temperature. The mixture was poured into water. The organic phase was washed with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography using a 5:2 mixture of hexane and ethyl acetate as eluent. There was thus obtained (2RS,3SR)-3-hydroxy-2-methyl-3-(2-methylthiothien-4-yl)tetrahydrofuran (4.05 g, 63%). NMR Spectrum 1.1 (d, 3H), 2.0 (s, 1H), 2.2 (m, 1H), 2.5 (m, 4H), 3.9-4.2 (m, 3H), 7.0-7.2 (m, 2H).

Reference： [1]Patent: US5332757,1994,A

41
[ 3188-00-9 ]
[ 912957-58-5 ]
(2RS,3SR)-N-(6-(2-(2-methyl-tetrahydrofuran-3-ylamino)-4-(trifluoromethyl)phenyl)pyrimidin-4-yl)benzo[d]thiazol-6-amine [ No CAS ]
(2RS,3RS)-N-(6-(2-(2-methyl-tetrahydrofuran-3-ylamino)-4-(trifluoromethyl)phenyl)pyrimidin-4-yl)benzo[d]thiazol-6-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 7; (2R,S, 3R,S)-N-(6-(2-(2-Methyl-tetrahydrofuran-3-ylamino)-4-(trifluoromethyl)phenyl)pyrimidin-4-yl)benzo[d]thiazol-6-amine. To a 100-mL, round-bottomed flask equipped with reflux condenser and Dean-Stark trap, were added N-(6-(2-amino-4-(trifluoromethyl)phenyl)pyrimidin-4-yl)benzo[d]-thiazol-6-amine (300 mg, 0.77 mmol, prepared as described in WO 03/099284), <strong>[3188-00-9]2-methyltetrahydrofuran-3-one</strong> (194 mg, 1.94 mmol, Aldrich), 4-methylbenzene-sulfonic acid hydrate (74 mg, 0.39 mmol, Aldrich) and toluene (40 mL). The reaction mixture was heated to reflux for 1 h, cooled to 70 C., and diluted with ethanol (10 mL). After the addition of NaCNBH3 (243 mg, 3.87 mmol, Aldrich), the reaction mixture was stirred at 70 C. for 1 h, and at room temperature for 12 h. The reaction mixture was evaporated under reduced pressure, and the residue was diluted with satd aqueous solution of NaHCO3 and extracted with EtOAc. The organic extract was washed with brine, dried over MgSO4, filtered, and evaporated under reduced pressure. The oily residue was purified by silica gel column chromatography (gradient: 2-5% MeOH/DCM) to provide yellow solid (100 mg). The solid was further purified by preparative HPLC [gradient 10-90% MeCN (0.1% TFA)/ H2O (0.1% TFA)] to give the title compound as a mixture of diastereoisomers. The product was isolated as a yellow amorphous solid. MS (ESI, pos. ion) m/z: 472 (M+1).

Reference： [1]Patent: US2006/235036,2006,A1 .Location in patent: Page/Page column 42

42
[ 3188-00-9 ]
ammonium chloride [ No CAS ]
(2RS,3SR)-3-(5-benzyloxypyrid-3-yl)-3-hydroxy-2-methyltetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With n-butyllithium; In diethyl ether; hexane;	A solution of a portion (11.5 g) of this product in diethyl ether (500 ml) was cooled to -50 C. and n-butyl-lithium (1.5M in hexane, 32 ml) was added dropwise. The mixture was stirred at -50 C. for 20 minutes, further cooled to -60 C. and a solution of <strong>[3188-00-9]2-methyltetrahydrofuran-3-one</strong> (5 g) in diethyl ether (50 ml) was added. The mixture was stirred at -60 C. for 1 hour and at -30 C. for 30 minutes. A saturated aqueous ammonium chloride solution (200 ml) was added and the mixture was extracted with ethyl acetate (3*50 ml). The combined organic extracts were washed with a saturated aqueous sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by column chromatography using a 7:3 v/v mixture of toluene and ethyl acetate as eluent. There was thus obtained (2RS,3SR)-3-(5-benzyloxypyrid-3-yl)-3 -hydroxy-2-methyltetrahydrofuran (7.8 g, 63%), as an oil; the 2-methyl and 3-hydroxy groups being in a cis-relationship. NMR Spectrum (CDCl3, delta values) 1.1(d, 3H), 2.3-2.8(m, 2H), 3.8-4.3(m, 3H), 5.1(s, 2H), 7.35(s, 5H), 7.6(m, 1H), 8.3(m, 2H).

Reference： [1]Patent: US5098930,1992,A

43
[ 7439-95-4 ]
[ 3188-00-9 ]
(2RS,3SR)-3-ethoxy-3-(5-fluoro-3-hydroxyphenyl)-2-methyltetrahydrofuran [ No CAS ]
[ 130722-44-0 ]
(2RS,3SR)-3-(3-benzyloxy-5-fluorophenyl)-3-hydroxy-2-methyltetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	In tetrahydrofuran;	The (2RS,3SR)-3-ethoxy-3-(5-fluoro-3-hydroxyphenyl)-2-methyltetrahydrofuran used as a starting material was obtained as follows: A Grignard reagent was prepared by heating a mixture of 3-benzyloxy-5-fluorophenyl bromide (4.2 g), magnesium powder (0.365 g) and tetrahydrofuran (20 ml) to 40 C. for 1 hour. The reagent was cooled to ambient temperature and <strong>[3188-00-9]2-methyltetrahydrofuran-3-one</strong> (1.16 ml) was added dropwise. The mixture was stirred at ambient temperature for 3 hours and then partitioned between ethyl acetate and water. The organic layer was washed with water, dried (MgSO4) and evaporated. The residue was purified by column chromatography using a 19:1 v/v mixture of methylene chloride and diethyl ether as eluent. There was thus obtained (2RS,3SR)-3-(3-benzyloxy-5-fluorophenyl)-3-hydroxy-2-methyltetrahydrofuran (2.3 g, 64%), m.p. 83-84 C.; the 2-methyl and 3-hydroxy groups being in a cis-relationship.
64%	In tetrahydrofuran;	b. The (2RS,3SR)-3-ethoxy-3-(5-fluoro-3-hydroxyphenyl)-2-methyltetrahydrofuran, used as a starting material, was obtained as follows: A Grignard reagent was prepared by heating a mixture of 3-benzyloxy-5-fluorophenyl bromide (4.2 g), magnesium powder (0.365 g) and tetrahydrofuran (20 ml) to 40 C. for 1 hour. The reagent was cooled to ambient temperature and <strong>[3188-00-9]2-methyltetrahydrofuran-3-one</strong> (1.16 ml) was added dropwise. The mixture was stirred at ambient temperature for 3 hours and then partitioned between ethyl acetate and water. The organic layer was washed with water, dried (MgSO4) and evaporated. The residue was purified by column chromatography using a 19:1 v/v mixture of methylene chloride and diethyl ether as eluent. There was thus obtained (2RS,3SR)-3-(3-benzyloxy-5-fluorophenyl)-3-hydroxy-2-methyltetrahydrofuran (2.3 g, 64%), m.p. 83-84 C.; the 2-methyl and 3-hydroxy groups being in a cis-relationship.

Reference： [1]Patent: US5098930,1992,A
[2]Patent: US5134148,1992,A

44
[ 3188-00-9 ]
2-methyl[4,5H]-dihydrofuran-3-thiol [ No CAS ]
[ 28588-74-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; hydrogen sulfide; sodium hydrogencarbonate; In diethyl ether; diethylene glycol dimethyl ether; water;	EXAMPLE IV Production of Furan-3-Thiol Derivatives A 250 ml flask fitted with a mechanical stirrer, gas inlet tube, calcium chloride drying tube, thermometer, and Y-tube is charged with 50 ml of distilled Diglyme, and the Diglyme is saturated with gaseous hydrogen chloride at 0-5 C with constant stirring. The flask is then immersed in a dry ice-isopropanol bath at -80 C. The cooled flask is charged with 14.0 g (0.14 mole) of 2-methyl-3-tetrahydrofuranone, and 28.5 g (0.84 mole) of hydrogen sulfide which has been chilled to -80 C is slowly warmed and allowed to boil over into the reaction flask. About one-half hour after the beginning of the hydrogen sulfide addition a pink-red color begins to appear in the reaction mixture. by the end of the 2.5 hours required for the addition of all the hydrogen sulfide, the reaction mixture is orange in color. At this time stirring is stopped, and the reaction mixture is permitted to stand 16 hours. A 1-liter Erlenmeyer flask is charged with sufficient sodium bicarbonate to cover the bottom of the flask and is placed into a dry ice-isopropanol bath. The reaction mixture is then poured slowly over the sodium bicarbonate to minimize foaming. Additional sodium bicarbonate is added until all foaming ceases. The neutralized mixture is treated with 200 ml of water and quickly extracted with 100 ml of methylene chloride. The organic solution so obtained is dried and concentrated to provide 39.5 grams of an oil. The oil is distilled under vacuum to provide a first cut taken at 73-80 C at 57 mm Hg and a second cut at 80-83 C at the same pressure. The 25 ml of the second portion is dissolved in 100 ml of ethyl ether and extracted four times with 5 ml of 5% aqueous sodium hydroxide to remove the pink color. The basic fraction so obtained is acidified with 11.2 cc of hydrochloric acid and extracted twice with 10 ml of ethyl ether, dried over sodium sulfate, and concentrated. This concentrate is then chromatographed to separate the 2-methylfuran-3-thiol and 2-methyl-[4,5H]dihydrofuran-3-thiol produced. These thiols have a roast meat aroma with the aroma of the furan-3-thiol being very similar to that of the disulfide produced in Example III. The analytical data on the 2-methylfuran-3-thiol are:

Reference： [1]Patent: US4020175,1977,A

45
[ 52-90-4 ]
[ 1262683-58-8 ]
[ 59-43-8 ]
[ 3188-00-9 ]
[ 40789-98-8 ]
[ 67633-97-0 ]
⁽¹³⁾C₅H₄O₂ [ No CAS ]
⁽¹³⁾C₅H₁₀OS [ No CAS ]
⁽¹³⁾C₅H₆OS [ No CAS ]
⁽¹³⁾C₅H₆OS [ No CAS ]
⁽¹³⁾C₆H₈OS [ No CAS ]
[ 63012-97-5 ]
[ 28588-74-1 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2007,vol. 55,p. 1552 - 1556

46
[ 52-90-4 ]
[ 1262683-58-8 ]
[ 59-43-8 ]
[ 3188-00-9 ]
[ 40789-98-8 ]
[ 67633-97-0 ]
⁽¹³⁾C₅H₁₀OS [ No CAS ]
⁽¹³⁾C₅H₆OS [ No CAS ]
⁽¹³⁾C₅H₆OS [ No CAS ]
C⁽¹³⁾C₅H₈OS [ No CAS ]
⁽¹³⁾C₆H₈OS [ No CAS ]
[ 63012-97-5 ]
[ 28588-74-1 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2007,vol. 55,p. 1552 - 1556

47
[ 1262683-58-8 ]
[ 59-43-8 ]
[ 74015-70-6 ]
[ 137-00-8 ]
[ 3188-00-9 ]
[ 40789-98-8 ]
[ 67633-97-0 ]
⁽¹³⁾C₅H₁₀OS [ No CAS ]
⁽¹³⁾C₅H₆OS [ No CAS ]
[ 28588-74-1 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2007,vol. 55,p. 1552 - 1556

48
[ 58-86-6 ]
[ 52-90-4 ]
[ 59-43-8 ]
[ 98-01-1 ]
[ 137-00-8 ]
[ 3188-00-9 ]
[ 40789-98-8 ]
[ 67633-97-0 ]
[ 98-02-2 ]
[ 63012-97-5 ]
[ 28588-74-1 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2007,vol. 55,p. 1552 - 1556
[2]Journal of Agricultural and Food Chemistry,2007,vol. 55,p. 1552 - 1556
[3]Journal of Agricultural and Food Chemistry,2007,vol. 55,p. 1552 - 1556

49
[ 58-86-6 ]
[ 52-90-4 ]
[ 59-43-8 ]
[ 74015-70-6 ]
[ 137-00-8 ]
[ 3188-00-9 ]
[ 40789-98-8 ]
[ 67633-97-0 ]
[ 98-02-2 ]
[ 63012-97-5 ]
[ 28588-74-1 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2007,vol. 55,p. 1552 - 1556

50
[ 58-86-6 ]
[ 59-43-8 ]
[ 74015-70-6 ]
[ 137-00-8 ]
[ 3188-00-9 ]
[ 40789-98-8 ]
[ 67633-97-0 ]
[ 28588-74-1 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2007,vol. 55,p. 1552 - 1556

51
[ 3188-00-9 ]
[ 178425-56-4 ]
2-methyl-3-(2-phenylcycloprop-1-enyl)tetrahydrofuran-3-ol [ No CAS ]

Reference： [1]Organic Letters,2011,vol. 13,p. 4076 - 4079

52
[ 3188-00-9 ]
C₁₆H₂₃NO₄S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7314 - 7321

53
[ 3188-00-9 ]
C₁₄H₁₉NO₄S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7314 - 7321

54
[ 3188-00-9 ]
[ 1415150-22-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7314 - 7321

55
[ 3188-00-9 ]
[ 1415150-23-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7314 - 7321

56
[ 3188-00-9 ]
[ 111-27-3 ]
C₁₁H₁₈O₂ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 5902 - 5916

57
[ 3188-00-9 ]
[ 41763-99-9 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 1403 - 1409

58
[ 3188-00-9 ]
[ 1609540-58-0 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 1403 - 1409

59
[ 3188-00-9 ]
2-methyltetrahydrofuran-3-ol [ No CAS ]
2-methyltetrahydrofuran-3-ol [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 12835 - 12842

60
[ 3188-00-9 ]
[ 86170-45-8 ]
benzyl (R)-3-(2-methyl-3-oxotetrahydrofuran-2-yl)propanoate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 4457 - 4463

61
[ 3188-00-9 ]
[ 25195-89-5 ]
1-methyl-9-methylene-2,6-dioxaspiro[4.5]decane [ No CAS ]
1-methyl-9-methylene-2,6-dioxaspiro[4.5]decane [ No CAS ]
C₁₀H₁₆O₂ [ No CAS ]
1,9-dimethyl-2,6-dioxaspiro[4.5]dec-9-ene [ No CAS ]
1,9-dimethyl-2,6-dioxaspiro[4.5]dec-9-ene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 10123 - 10131

62
[ 3188-00-9 ]
[ 25195-89-5 ]
1-methyl-9-methylene-2,6-dioxaspiro[4.5]decane [ No CAS ]
1,9-dimethyl-2,6-dioxaspiro[4.5]dec-9-ene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 10123 - 10131

63
[ 3188-00-9 ]
[ 100-52-7 ]
[ 109-77-3 ]
5-amino-3-methyl-7-phenyl-1,3-dihydroisobenzofuran-4,6-dicarbonitrile [ No CAS ]